tert-Butyl N-(thio-phen-2-yl)carbamate.

In the title compound, C9H13NO2S, the dihedral angle between the thiophene ring and the carbamate group is 15.79 (14)°. In the crystal structure, intra-molecular C-H⋯O inter-actions in tandem with the tert-butyl groups render the packing of adjacent mol-ecules in the [001] direction nearly perpendicular [the angle between adjacent thio-phene rings is 74.83 (7)°]. An inter-molecular N-H⋯O hydrogen bond gives rise to a chain extending along [001]. The crystal studied was found to be a racemic twin.

Related literature

For the synthesis of the title compound, see: Binder et al. (1977 ▶); Kruse et al. (1989 ▶). For related structures, see: Arsenyan et al. (2008 ▶); Elshaarawy & Janiak (2011 ▶); Low et al. (2009 ▶); Hsu et al. (2013 ▶).

Experimental

Crystal data

C9H13NO2S

M = 199.26

Orthorhombic,

a = 11.732 (2) Å

b = 8.6513 (17) Å

c = 9.879 (2) Å

V = 1002.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 153 K

0.20 × 0.10 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.944, T max = 0.977

2112 measured reflections

2112 independent reflections

1816 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.078

S = 1.04

2112 reflections

125 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack x determined using 703 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons & Flack, 2004 ▶)

Absolute structure parameter: 0.53 (4)

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: COLLECT; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, enCIFer (Allen et al., 2004 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681302196X/zs2273sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302196X/zs2273Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681302196X/zs2273Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H13NO2S	Dx = 1.320 Mg m−3
Mr = 199.26	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 1327 reflections
a = 11.732 (2) Å	θ = 1.0–27.5°
b = 8.6513 (17) Å	µ = 0.29 mm−1
c = 9.879 (2) Å	T = 153 K
V = 1002.7 (3) Å3	Rod, colorless
Z = 4	0.20 × 0.10 × 0.08 mm
F(000) = 424

Nonius KappaCCD diffractometer	2112 independent reflections
Radiation source: fine-focus sealed tube	1816 reflections with I > 2σ(I)
φ and ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997)	h = −15→15
Tmin = 0.944, Tmax = 0.977	k = −11→11
2112 measured reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.078	w = 1/[σ2(Fo2) + (0.0301P)2 + 0.2397P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2112 reflections	Δρmax = 0.25 e Å−3
125 parameters	Δρmin = −0.19 e Å−3
2 restraints	Absolute structure: Flack x determined using 703 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004).
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.53 (4)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
S1	0.13622 (6)	0.05380 (7)	0.63359 (7)	0.02745 (19)
O1	0.29399 (16)	0.2992 (2)	0.61913 (19)	0.0273 (4)
O2	0.32467 (18)	0.4564 (2)	0.80079 (18)	0.0289 (5)
N1	0.23352 (19)	0.2367 (2)	0.8305 (2)	0.0224 (5)
H1N	0.238 (3)	0.264 (4)	0.919 (2)	0.036 (9)*
C1	0.1713 (2)	0.1041 (3)	0.7987 (3)	0.0209 (5)
C2	0.1219 (3)	0.0067 (3)	0.8902 (3)	0.0241 (6)
H2	0.1317	0.0150	0.9854	0.029*
C3	0.0542 (2)	−0.1082 (3)	0.8269 (3)	0.0289 (6)
H3	0.0137	−0.1855	0.8754	0.035*
C4	0.0533 (3)	−0.0964 (3)	0.6907 (3)	0.0306 (7)
H4	0.0115	−0.1635	0.6329	0.037*
C5	0.2857 (2)	0.3295 (3)	0.7389 (3)	0.0220 (6)
C6	0.3798 (2)	0.5829 (3)	0.7233 (3)	0.0250 (6)
C7	0.3034 (3)	0.6385 (4)	0.6108 (4)	0.0438 (9)
H7A	0.2928	0.5554	0.5446	0.066*
H7B	0.3384	0.7280	0.5663	0.066*
H7C	0.2292	0.6684	0.6483	0.066*
C8	0.4940 (3)	0.5271 (4)	0.6722 (4)	0.0445 (9)
H8A	0.5384	0.4856	0.7480	0.067*
H8B	0.5354	0.6135	0.6310	0.067*
H8C	0.4823	0.4458	0.6045	0.067*
C9	0.3945 (3)	0.7083 (3)	0.8284 (4)	0.0459 (9)
H9A	0.3196	0.7408	0.8617	0.069*
H9B	0.4337	0.7970	0.7878	0.069*
H9C	0.4399	0.6685	0.9040	0.069*

	U11	U22	U33	U12	U13	U23
S1	0.0369 (4)	0.0261 (3)	0.0194 (3)	−0.0050 (3)	0.0003 (3)	−0.0034 (3)
O1	0.0377 (11)	0.0268 (9)	0.0173 (10)	−0.0043 (8)	0.0014 (9)	−0.0012 (8)
O2	0.0425 (12)	0.0258 (10)	0.0182 (9)	−0.0120 (8)	0.0029 (9)	0.0003 (8)
N1	0.0293 (13)	0.0232 (11)	0.0147 (9)	−0.0051 (9)	0.0006 (10)	−0.0009 (10)
C1	0.0234 (13)	0.0211 (12)	0.0183 (12)	0.0033 (11)	0.0000 (11)	−0.0012 (11)
C2	0.0277 (16)	0.0226 (13)	0.0221 (13)	0.0002 (11)	−0.0017 (11)	0.0006 (11)
C3	0.0300 (16)	0.0227 (14)	0.0340 (15)	−0.0037 (12)	−0.0002 (13)	0.0029 (13)
C4	0.0329 (18)	0.0259 (15)	0.0330 (15)	−0.0030 (12)	−0.0029 (14)	−0.0039 (13)
C5	0.0238 (15)	0.0227 (14)	0.0195 (15)	0.0016 (11)	−0.0023 (11)	−0.0005 (11)
C6	0.0288 (17)	0.0228 (14)	0.0234 (13)	−0.0047 (12)	0.0053 (11)	0.0019 (11)
C7	0.0453 (19)	0.0306 (15)	0.056 (2)	−0.0046 (14)	−0.0128 (18)	0.0135 (16)
C8	0.0299 (17)	0.0339 (16)	0.070 (2)	−0.0022 (13)	0.0128 (18)	0.0021 (16)
C9	0.070 (2)	0.0327 (17)	0.0347 (17)	−0.0212 (17)	0.0122 (17)	−0.0068 (15)

S1—C4	1.718 (3)	C4—H4	0.9500
S1—C1	1.737 (3)	C6—C7	1.507 (4)
O1—C5	1.216 (3)	C6—C8	1.511 (4)
O2—C5	1.337 (3)	C6—C9	1.512 (4)
O2—C6	1.484 (3)	C7—H7A	0.9800
N1—C5	1.356 (3)	C7—H7B	0.9800
N1—C1	1.396 (3)	C7—H7C	0.9800
N1—H1N	0.90 (2)	C8—H8A	0.9800
C1—C2	1.365 (4)	C8—H8B	0.9800
C2—C3	1.418 (4)	C8—H8C	0.9800
C2—H2	0.9500	C9—H9A	0.9800
C3—C4	1.350 (4)	C9—H9B	0.9800
C3—H3	0.9500	C9—H9C	0.9800
C4—S1—C1	90.88 (14)	C7—C6—C8	112.6 (3)
C5—O2—C6	121.3 (2)	O2—C6—C9	103.0 (2)
C5—N1—C1	124.9 (2)	C7—C6—C9	110.2 (3)
C5—N1—H1N	117 (2)	C8—C6—C9	111.0 (3)
C1—N1—H1N	118 (2)	C6—C7—H7A	109.5
C2—C1—N1	125.4 (2)	C6—C7—H7B	109.5
C2—C1—S1	111.5 (2)	H7A—C7—H7B	109.5
N1—C1—S1	122.77 (19)	C6—C7—H7C	109.5
C1—C2—C3	112.2 (3)	H7A—C7—H7C	109.5
C1—C2—H2	123.9	H7B—C7—H7C	109.5
C3—C2—H2	123.9	C6—C8—H8A	109.5
C4—C3—C2	113.0 (3)	C6—C8—H8B	109.5
C4—C3—H3	123.5	H8A—C8—H8B	109.5
C2—C3—H3	123.5	C6—C8—H8C	109.5
C3—C4—S1	112.3 (2)	H8A—C8—H8C	109.5
C3—C4—H4	123.8	H8B—C8—H8C	109.5
S1—C4—H4	123.8	C6—C9—H9A	109.5
O1—C5—O2	126.4 (2)	C6—C9—H9B	109.5
O1—C5—N1	123.9 (2)	H9A—C9—H9B	109.5
O2—C5—N1	109.6 (2)	C6—C9—H9C	109.5
O2—C6—C7	110.9 (2)	H9A—C9—H9C	109.5
O2—C6—C8	108.8 (2)	H9B—C9—H9C	109.5
C5—N1—C1—C2	177.5 (3)	C1—S1—C4—C3	−0.9 (3)
C5—N1—C1—S1	−8.9 (4)	C6—O2—C5—O1	3.3 (4)
C4—S1—C1—C2	0.9 (2)	C6—O2—C5—N1	−176.4 (2)
C4—S1—C1—N1	−173.5 (2)	C1—N1—C5—O1	−7.8 (4)
N1—C1—C2—C3	173.6 (2)	C1—N1—C5—O2	171.9 (2)
S1—C1—C2—C3	−0.7 (3)	C5—O2—C6—C7	54.5 (3)
C1—C2—C3—C4	0.0 (4)	C5—O2—C6—C8	−69.8 (3)
C2—C3—C4—S1	0.7 (4)	C5—O2—C6—C9	172.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.90 (2)	2.04 (2)	2.920 (3)	165 (3)
C7—H7A···O1	0.98	2.33	2.938 (4)	119
C8—H8C···O1	0.98	2.55	3.109 (4)	116

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.90 (2)	2.04 (2)	2.920 (3)	165 (3)
C7—H7A⋯O1	0.98	2.33	2.938 (4)	119
C8—H8C⋯O1	0.98	2.55	3.109 (4)	116

Symmetry code: (i) .